N-(substituted amino)pyrrole derivatives, and herbicidal compositions

Abstract

This invention is to provide an N-(substituted amino)pyrrole derivative represented by the formula (I): which is used as an effective ingredient of herbicidal compositions: ##STR1## wherein R 2 , R 3 , R 4 and R 5 is independently hydrogen atom, halogen atom, C 1 -C 4 alkyl group, (C 1 -C 4 alkyl)carbonyl group, (C 3 -C 6 cycloalkyl) carbonyl group, (C 1 -C 4 haloalkyl)carbonyl group, (C 3 -C 5 alkenyl)carbonyl group, benzoyl group which may be substituted with 1-3 halogen atoms and/or C 1 -C 4 alkyl groups, N,N-[(di-C 1 -C 4 alkyl)amino]carbonyl group, (C 1 -C 4 alkoxy)carbonyl group, etc., X 1 and X 2 are independently hydrogen atom, halogen atom, C 1 -C 4 alkyl group, C 1 -C 4 alkoxy group, etc., and Z is nitrogen atom or CH.

What is claimed is: 
     
       1. An N-(substituted amino)pyrrole derivative represented by the formula (I): ##STR11## wherein R 2 , R 3 , R 4  and R 5  is independently hydrogen atom, halogen atom, C 1  -C 4  alkyl group, C 1  -C 5  haloalkyl group, C 2  -C 5  alkoxyalkyl group, C 3  -C 5  alkenyl group, C 3  -C 5  haloalkenyl group, C 3  -C 5  alkinyl group, phenyl group which may be substituted with 1-3 halogen atoms and/or C 1  -C 4  alkyl groups, C 7  -C 9  aralkyl group which may be substituted with 1-3 halogen atoms and/or C 1  -C 4  alkyl groups, (C 1  -C 4  alkyl)carbonyl group, (C 2  -C 5  alkoxyalkyl)carbonyl group, (C 3  -C 6  cycloalkyl)carbonyl group, (C 1  -C 4  haloalkyl)carbonyl group, (C 3  -C 5  alkenyl)carbonyl group, benzoyl group which may be substituted with 1-3 halogen atoms and/or C 1  -C 4  alkyl groups, (C 7  -C 9  aralkyl)carbonyl group which may be substituted with 1-3 halogen atoms and/or C 1  -C 4  alkyl groups, carbamoyl group, N-(C 1  -C 4  alkyl)aminocarbonyl group, N,N-[(di-C 1  -C 4  alkyl)amino]carbonyl group, carboxyl group, (C 1  -C 4  alkoxy)carbonyl group, (C 1  -C 4  haloalkoxy)carbonyl group, (C 2  -C 5  alkoxyalkoxy)carbonyl group, (C 3  -C 5  alkenyloxy)carbonyl group, (C 3  -C 5  haloalkenyloxy)carbonyl group or (C 3  -C 5  alkynyloxy)carbonyl group; R 6  is hydrogen atom, C 1  -C 5  alkyl group, C 1  -C 5  haloalkyl group, C 2  -C 5  alkoxyalkyl group, C 3  -C 5  alkenyl group, C 3  -C 5  haloalkenyl group, C 3  -C 5  alkynyl group or C 7  -C 9  aralkyl group which may be substituted with 1-3 halogen atoms and/or C 1  -C 4  alkyl groups;   X 1  and X 2  are independently hydrogen atom, halogen atom, C 1  -C 4  alkyl group, C 1  -C 4  alkoxy group, C 1  -C 4  alkylthio group, C 1  -C 4  haloalkyl group, C 1  -C 4  haloalkoxy group, C 1  -C 4  haloalkylthio group, C 2  -C 4  alkoxyalkyl group, C 2  -C 4  thioalkoxyalkyl group or NR 7  R 8  wherein R 7  and R 8  are independently hydrogen atom, C 1  -C 4  alkyl group or C 1  -C 4  alkoxy group; and   Z is nitrogen atom.   
     
     
       2. An N-(substituted amino)pyrrole derivative of claim 1, wherein X 1  and X 2  are independently halogen, C 1  -C 2  alkyl, ethoxy, i-propoxy, methoxy, sec-butoxy, C 1  -C 2  fluoroalkyl, C 1  -C 2  fluoroalkoxy, C 2  -C 4  alkoxyalkyl or NR 7  R 8 , wherein R 7  and R 8  are independently hydrogen or C 1  -C 2  alkyl. 
     
     
       3. An N-(substituted amino) pyrrole derivative of claim 1, wherein R 6  is hydrogen, methyl, ethyl, i-propyl, n-butyl, 2,2,2-trifluoroethyl, 3-methoxypropyl, crotyl, propargyl, 3,3-dichloroallyl, benzyl, 4-chlorobenzyl or 4-methylbenzyl. 
     
     
       4. An N-(substituted amino) pyrrole derivative of claim 1, wherein R 3 , R 4  and R 5  are hydrogens, R 2 , R 4  and R 5  are hydrogens or R 3  and R 4  are hydrogens. 
     
     
       5. An N-(substituted amino) pyrrole derivative of claim 1, wherein R 3 , R 4  and R 5  are hydrogens, R 2 , R 4  and R 5  are hydrogens or R 3  and R 4  are hydrogens; R 6  is hydrogen, methyl, ethyl, i-propyl, n-butyl, 2,2,2-trifluoroethyl, 3-methoxypropyl, crotyl, propargyl, 3,3-dichloroallyl, benzyl, 4-chlorobenzyl or 4-methoxybenzyl, X 1  and X 2  are independently halogen, C 1  -C 2  alkyl, ethoxy, i-propoxy, methoxy, sec-butoxy, C 1  -C 2  fluoroalkyl, C 1  -C 2  fluoroalkoxy, C 2  -C 4  alkoxyalkyl or NR 7  R 8 , wherein R 7  and R 8  are independently hydrogen or C 1  -C 2  alkyl. 
     
     
       6. An N-(substituted amino) pyrrole derivative of claim 1, wherein R 3 , R 4  and R 5  are hydrogens and R 2  is hydrogen, bromine, methyl, acetyl, propionyl, cyclopropanecarbonyl, trifluoroacetyl, 4-chlorobutyryl, benzoyl, dimethylcarbamoyl or methoxycarbonyl; or R 2  and R 5  are methyls and R 3  and R 4  are hydrogens; R 6  is hydrogen or methyl; X 1  and X 2  are independently chlorine, methyl or methoxy. 
     
     
       7. A herbicidal composition which comprises a herbicidally effective amount of an N-(substituted amino)-pyrrole derivative of claim 1 and an agronomically-acceptable carrier or diluent.